ChatGPT

ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

By Sean O'Shaughnessey

A few days ago, a sales manager asked me which AI platform to use for writing cold emails. I told him it depends on what kind of emails he’s writing, and he looked confused. That confusion is common and costly. ChatGPT, Claude, Gemini, and Copilot all look similar at first glance, but in reality, they serve very different purposes depending on your sales workflow.

Choosing the right platform matters because the wrong choice drains time, creates change fatigue, and erodes ROI. Companies that align platform strengths to sales use cases are seeing dramatic results: 40% higher email response rates, 60% faster proposal generation, and triple the efficiency in call preparation. The stakes are high, and the decision deserves more than guesswork.

ChatGPT: The Versatile Performer
ChatGPT shines when creativity and personality are critical. It’s excellent for cold emails with humor, social selling posts, objection-handling scripts, and meeting prep. The downside? It can be verbose and sometimes casual for executive communication. If your team thrives on creativity and prospecting with personality, ChatGPT is a strong choice.

Claude: The Professional Communicator
Claude specializes in polished, business-appropriate communication. It’s strong for executive proposals, deal analysis, contract prep, and professional email sequences. While less creative than ChatGPT, it’s ideal for enterprise and strategic sales where tone, nuance, and professionalism are paramount.

Gemini: The Integrated Researcher
Google’s Gemini offers real-time research, market intelligence, and smooth integration with Google Workspace. It’s especially powerful for sales teams who rely heavily on spreadsheets, Gmail, and real-time prospect research. However, it may produce generic copy and come with potential data privacy concerns.

Copilot: The Enterprise Integrator
Microsoft Copilot excels in environments already standardized on Microsoft tools. Its strength lies in Outlook automation, PowerPoint proposals, Teams prep, and CRM integrations. While it can feel corporate and less creative, it’s perfect for organizations that value compliance, governance, and seamless integration across Microsoft 365.

Making the Right Choice
The best AI platform isn’t the one with the flashiest marketing; it’s the one your team will consistently use. Start by mapping your use cases: creative outreach, professional communication, research, or enterprise integration. Then run pilot programs, measure results, and refine your approach. Many sales teams find value in using more than one platform, each aligned to a different stage of the sales cycle.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Let’s build that future together.

If you’d like to explore this topic in more depth, there’s a podcast episode that covers all of this information and more. You can find the link below and consider subscribing to the podcast AI Tool for Sales Pros on your favorite podcast player.

Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

By Sean O'Shaughnessey

Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it’s a wake-up call, a roadmap, and a motivational boost for anyone in the world of revenue generation, sales processes, and messaging strategy.

Whether you’re a frontline salesperson or a VP of sales leading a team, this conversation will inspire you to rethink how you work, what skills future-proof your career, and how AI can become your competitive advantage instead of your competitor.

Key Topics Discussed

The 4 Irreplaceable Skills That Safeguard Sales Careers (01:00)
Sean breaks down a framework for evaluating whether your job is AI-proof, hint: if you’re in B2B sales and good at it, you’re likely already building a durable edge.
How AI Mirrors the Arrival of the Internet in Sales Evolution (04:10)
Kevin draws a compelling parallel between today’s AI landscape and the early days of the internet, showing why this shift is just as transformative.
Sales Management and Strategic Value in an AI World (02:46 & 07:31)
From leadership and team building to messaging and workflow design, the episode highlights why sales managers need to think beyond quotas and towards long-term enablement.
A Personal Story of Old-School Sales and the Power of Adapting Tools (08:00)
Sean shares a nostalgic (and relevant) story about his father’s sales career before personal computers, offering perspective on how sales adapts across generations.
Weaponizing Your Time: Using AI to Amplify Human Strengths (13:00)
Kevin delivers a call to action on how to audit your own sales day and offload low-value tasks through automation, freeing up more time for high-impact strategy and consultation.

Key Quotes

“You won’t lose your job to AI, you’ll lose your job to a better salesperson who uses AI.”
– Sean O’Shaughnessey (01:02)
“If you’re not using AI, or any sales technology, you’re not doing your job. You’re underperforming.”
– Kevin Lawson (06:11)
“Sales worked before computers, and it will work after AI. What changes is how well you adapt the tools available.”
– Sean O’Shaughnessey (10:04)
“Your time is your greatest asset, and your biggest liability, when you’re not using it to its highest utility.”
– Kevin Lawson (14:00)

Additional Resources

Sean’s original blog post on this topic (available in the B2B Sales Lab and LinkedIn) https://newsales.expert/2025/06/b2b-sales-in-the-age-of-ai-why-top-salespeople-will-thrive-while-the-repetitive-roles-disappear/
B2B Sales Lab community discussion on sales evolution and AI https://b2b-sales-lab.com/
Tools mentioned: ChatGPT, Perplexity, Gemini (as starting points for AI integration)

A Significant Actionable Item from this Podcast

Audit your sales day for repeatable, low-value tasks that can be automated.
Pick one of them, like researching prospects, summarizing meeting notes, or drafting follow-ups, and replace it with an AI tool like ChatGPT or Perplexity. You’ll recover time, increase productivity, and move closer to building a modern, AI-augmented sales practice.

Final Summary

This episode of Two Tall Guys Talking Sales isn’t about fear, it’s about focus. Sales success today requires a sharp blend of strategic thinking, tool adoption, and human skills that are nearly impossible to replicate. Kevin and Sean lay out a blueprint that every sales leader, rep, and business owner should follow to thrive in this new era. If you’re serious about sales management, value selling, messaging clarity, and staying ahead of disruption, this episode will give you the mindset and tactical clarity to act now. Don’t just listen, level up.

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

By Sean O'Shaughnessey

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

Hard-to-automate skills
Deployment-related skills
Scarce, high-utility skills
Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

Read the rest of the article…

Two Tall Guys Talking Sales – From CRM to AI: Building Your Sales Toolbox – E113

By Sean O'Shaughnessey

In this episode of “Two Tall Guys Talking Sales,” Kevin Lawson and Sean O’Shaughnessey dive into the critical tools every modern salesperson needs to thrive. Whether you’re equipping yourself in a tech-limited environment or looking to amplify your selling power with affordable tools, Kevin and Sean share practical insights from their decades of experience in sales and technology. This episode is packed with actionable advice for sales professionals looking to streamline their workflows and close deals more efficiently.

Key Topics Discussed

[00:01:00] Taking Notes Efficiently: The duo discusses tools like Evernote, OneNote, and even native apps like Notes, emphasizing the importance of accessible, synchronized note-taking for sales success.
[00:03:00] CRM Essentials: Why Outlook or spreadsheets don’t cut it as CRMs and affordable alternatives like HubSpot and Insightly that can transform your sales process.
[00:05:00] Integration is Key: Kevin highlights how integrating tools like email, CRMs, and AI writing assistants such as ChatGPT or Claude can create a seamless selling experience.
[00:07:30] Managing Mileage and Expenses: Sean introduces tools like MileIQ and Expensify to streamline mileage tracking and expense management for busy salespeople.
[00:12:00] Staying Top of Mind: How CRMs help salespeople maintain relationships by tracking the timing and content of client interactions.

Key Quotes

Kevin [00:05:00]: “Integrate everything. All of your tools should talk to each other—most of that, you’ll find under the marketplace of your CRM.”
Sean [00:04:00]: “Outlook is not a CRM. Gmail is not a CRM. They’re just tools. A true CRM system will help you relate multiple people together at the same company and keep track of your progress.”
Kevin [00:13:30]: “When we write to reconnect, it’s not about us; it’s about them. The fewer times you say ‘I, me, or my’ in an email, the better your message will land.”

Additional Resources

HubSpot CRM: A free CRM option for individual salespeople to manage contacts and deals.
Insightly CRM: A free CRM option for individual salespeople to manage contacts and deals.
MileIQ: A mileage-tracking app that simplifies expense reporting.
Expensify: A freemium tool to manage receipts and expenses with ease.
ChatGPT and Claude: AI writing tools that improve email and content creation for sales professionals.
Grammarly: An AI-powered writing assistant that enhances communication by providing real-time feedback on grammar, clarity, tone, and style across various platforms and devices.

A Significant Actionable Item from this Podcast

Build your integrated tech stack now. Start by selecting a free CRM like HubSpot or Insightly, then add complementary tools for note-taking, mileage tracking, and email integration. Use AI tools like ChatGPT to refine your communications and ensure every tool in your stack works seamlessly.

Summary

Whether you’re a tech-savvy salesperson or just starting to explore the power of modern tools, this episode offers a roadmap for building an affordable, effective sales tech stack. Kevin and Sean provide real-world examples and practical advice to help you stay organized, build stronger client relationships, and close deals faster. Don’t miss this episode—it could be the catalyst for taking your sales game to the next level. Listen now!

Two Tall Guys Talking Sales Podcast – From SWOT to Success: Navigating the Competitive Sales Landscape – Episode 46

By Sean O'Shaughnessey

In this invigorating episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the realm of competition in sales. From understanding the various forms competition can take to harnessing the power of artificial intelligence in competitive analysis, this episode is packed with insights and actionable advice for sales professionals at all levels.

Key Topics Discussed:

The Essence of Competition in Sales: Why understanding and overcoming your competition is crucial.
Recognizing Different Types of Competition: Beyond direct competitors, why the ‘no decision’ outcome is the hidden enemy.
Leveraging SWOT Analysis: Sean and Kevin’s take on its relevance and how to use it effectively for competitive advantage.
The Role of Artificial Intelligence in Sales: How tools like Chat GPT can help get a leg up on your competition.
The Importance of Competitive Awareness: Why 57% of companies are at a disadvantage and how not to be one of them.

Key Quotes:

Kevin: “Every professional sports team watches game film… we’re sales professionals. We should be watching the game film of sorts.”
Sean: “Who is your prospect talking to? That is your competition.”
Kevin: “Doing nothing is unacceptable. It’s like prospecting. If you don’t prospect, that is an unacceptable behavior.”
Sean: “If you’re in a small company right now, you need to figure out, you need to be one of the 43%, not one of the 57%.”

Additional Resources:

Eliminate Your Competition by Sean O’Shaughnessey.
Sales Xceleration’s national research on companies’ competitive awareness.
Tools like Chat GPT for AI-based SWOT analysis.

Don’t be a part of the 57% that remains oblivious to their competition. Whether you’re in the early stages of your sales journey or a seasoned professional, Sean and Kevin’s insights from this episode offer invaluable strategies and tools to elevate your game. Tune in to “Two Tall Guys Talking Sales” to get the upper hand, understand your market better, and, ultimately, eliminate your competition.